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Compare 732 Vacation Homes in Chester with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (51)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.8 out of 10, Exceptional, (24)
The price is SAR 311
SAR 974 total
includes taxes & fees
1 Apr - 2 Apr

Modern Waterfront House with Amazing views!
Modern Waterfront House with Amazing views!

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
10.0 out of 10, Exceptional, (34)

Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (70)

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Waterfront Sunset Bayview: sleeps 6
Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, (12)

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
10.0 out of 10, Exceptional, (118)

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

Best Western Kent Narrows Inn
5/5 Excellent
"I would definitely stay here again"
A verified traveler from Lowell stayed at Best Western Kent Narrows Inn
Posted 2 days ago